Diazepam → Methyl 5-chloro-3-phenyl-2H-isoindole-1-carboxylate

HRID 1973288Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2N(C)C(=O)[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[CH3:21][O:22][C:23](=[O:26])OC>>[CH3:21][O:22][C:23]([C:9]1[NH:8][C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:6]2[C:5]=1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20]2)=[O:26]

Participants

Reactant 2

HCID 3016Diazepam

HCID 12021Dimethyl Carbonate

Product 1

HCID 53969048Methyl 5-chloro-3-phenyl-2H-isoindole-1-carboxylate

Procedure

The starting material can be prepared from 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one and dimethylcarbonate in a manner analogous to that described in Example 1. After recrystallization from acetone, there is obtained 5-chloro-3-phenylisoindole-1-carboxylic acid methyl ester; melting point 208°-210° C. (decomposition).

Workup

customAfter recrystallization from acetone

Sources & evidence

ORD record: ord-c114acc9d62b4995b63d17d4f47df13f
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03996374

Reaction notes

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